8-benzyl-6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-3H,7H-imidazo[1,2-a]pyrazin-3-one

• ChemBase ID: 126665
• Molecular Formular: C26H21N3O3
• Molecular Mass: 423.46324
• Monoisotopic Mass: 423.15829155
• SMILES: c1ccc(cc1)Cc1c2nc(c(=O)n2cc([nH]1)c1ccc(cc1)O)Cc1ccc(cc1)O
• Canonical SMILES: Oc1ccc(cc1)Cc1nc2n(c1=O)cc([nH]c2Cc1ccccc1)c1ccc(cc1)O
• InChI: InChI=1S/C26H21N3O3/c30-20-10-6-18(7-11-20)15-23-26(32)29-16-24(19-8-12-21(31)13-9-19)27-22(25(29)28-23)14-17-4-2-1-3-5-17/h1-13,16,27,30-31H,14-15H2
• InChIKey: YHIPILPTUVMWQT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 8-benzyl-6-(4-hydroxyphenyl)-2-[(4-hydroxyphenyl)methyl]-3H,7H-imidazo[1,2-a]pyrazin-3-one
• IUPAC Traditional name: coelenterazine
• Synonyms: Coelenterazine; Renilla luciferin; Coelenterazine; 3,2-Dihydro-2-(p-hydroxybenzyl)-6-(p-hydroxyphenyl)-8-benzylimidazolo[1,2-a]pyrazin-3-one; CLZN; Coelenterazine, native; 8-Benzyl-2-(4-hydroxybenzyl)-6-(4-hydroxyphenyl)imidazo[1,2-a]pyrazin-3(7H)-one; Coelenterazine; Luciferin, Preluciferin,; Coelenterazine, native

Database IDs

• CAS Number: 55779-48-1
• MDL Number: MFCD00467176
• PubChem SID: 162220995; 24892477
• PubChem CID: 2830
• CHEBI ID: 2311
• Chemspider ID: 2728
• Wikipedia Title: Coelenterazine

CALCULATED PROPERTIES

• Acid pKa: 9.17498
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 4.398724
• LogD (pH = 7.4): 4.391611
• Log P: 4.398828
• Molar Refractivity: 133.8918 cm^3
• Polarizability: 46.65655 Å^3
• Polar Surface Area: 85.16 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: methanol and ethanol: soluble
• Apperance: orange-yellow crystals; yellow solid; Yellow Solid
• Melting Point: 175-178°C
• Fluorescence: λex 400 nm; λem 514 nm in 0.1 M phosphate pH 7.0

Safety Information

• German water hazard class: 3
• GHS Hazard statements: H413
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Suitability: corresponds for UV spectrum
• Empirical Formula (Hill Notation): C26H21N3O3

DETAILS

Sigma Aldrich - C2230

Caution
Protect from exposure to light
Biochem/physiol Actions
Luminophore of the aequorin complex which is oxidized by oxygen to illuminate at 465 nm when Ca2+ binds to the complex; used to measure Ca2+ concentration in cells with high sensitivity and large dynamic range.

Sigma Aldrich - 07372

Other Notes
Assay of mitochondrial calcium flux; calcium fosters the decomposition to CO2 and coelenteramide with bioluminescence.

Toronto Research Chemicals - C636000

A luminophore of the aequorin complex which is oxidized by oxygen to illuminate at 465nm when Ca2+ binds to the complex. Used to measure Ca2+ concentration in cells with high sensitivity an dlarge dynamic range.

REFERENCES

• Fluck, R.A., et al.: J. Cell Biol., 115, 1259 (1991)
• Jones, K., et al.: Trends Biotechnol., 17, 477 (1991)
• Dubuisson, M.L., et al.: Biochem. Pharmacol., 60, 471 (2000)